House Hacking in Chicago...with a family

[Melina Dea]

Hello!  I'm interested in pursuing my real estate investment goals through house hacking. Typically this is done by young investors, however with a young family (two kids currently 4 and 2) I understand this is not the most conventional path and would like some feedback. Quick background: My husband and I live in Houston, TX and have been wanting to move for a few years now; but the downturn in the oil industry and our kids getting older are getting us eager to make a move. My husband can work from anywhere and I'd like to find a position working for a university, so we hope to move the summer of 2018. This gives us a chance to continue to save and figure out where we'd like to be.

Maybe it's my suburban upbringing, but the idea of pursuing this in an urban environment seems less sketchy, since most people are living in tighter quarters as it is. The path I keep coming back to is buying a multi-unit in Chicago (preferably a 3-unit) with my family in one, and renting out the other two.  I'd be looking on the north side, where it appears the public schools (at this point I'm focusing on elementary) are pretty good.  

The driver is to use real estate as a way to build wealth and achieve passive income.  After years of mortgage payments, car notes and daycare the thought of having a discounted mortgage, one (or zero!) car payments and public schools sounds wonderful.  I have a few potential exit strategies if this is not meant to be: A) use the equity in the home and convert the unit into a single family home B) rent all units and maintain as an income property C) if we decide this isn't for us - sell and return to our home in Houston (I'd like to rent this out while we're gone. Family is nearby and could help).

If anyone out there has done this (in Chicago or elsewhere) with kids in tow I'd love any feedback.  Recommendations of where this is achievable (zip codes or schools to look for) would be really helpful as well.  We've visited Chicago the last couple of years, but I'm by no means a local expert.  The ballpark price range is probably up to the mid $600's.  But at this point I'd like feedback more on along the lines of whether this is doable or if I've lost my mind. :)

Thanks in advance!